# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name ' Orde Munro' _publ_contact_author_email MUNROO@UKZN.AC.ZA loop_ _publ_author_name O.Munro N.R.Crouch S.E.Drewes 'K.du Toit' D.A.Mulholland data_ka2b _database_code_depnum_ccdc_archive 'CCDC 283813' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 25R,5beta-spirostane-1beta,3alpha-diol _chemical_melting_point ? _chemical_formula_moiety 'C27 H44 O4' _chemical_formula_sum 'C27 H44 O4' _chemical_formula_weight 432.62 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.4271(10) _cell_length_b 6.9958(19) _cell_length_c 15.189(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.054(11) _cell_angle_gamma 90.00 _cell_volume 1202.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2 _cell_measurement_theta_max 12 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method 'Omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 1 _diffrn_reflns_number 5466 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2310 _reflns_number_gt 2104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius CAD4' _computing_cell_refinement 'Nonius CAD4' _computing_data_reduction 'Nonius CAD4' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.0680P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2310 _refine_ls_number_parameters 292 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.10188(19) 0.6249(3) 0.15756(13) 0.0321(5) Uani 1 1 d . . . H1 H 0.0491 0.5461 0.1880 0.039 Uiso 1 1 calc R . . C2 C 0.04150(18) 0.8136(3) 0.13203(14) 0.0312(5) Uani 1 1 d . . . H2A H -0.0315 0.7901 0.0927 0.037 Uiso 1 1 calc R . . H2B H 0.0219 0.8763 0.1850 0.037 Uiso 1 1 calc R . . C3 C 0.1196(2) 0.9432(3) 0.08621(14) 0.0351(5) Uani 1 1 d . . . H3 H 0.1340 0.8842 0.0302 0.042 Uiso 1 1 calc R . . C4 C 0.2363(2) 0.9762(3) 0.14420(14) 0.0371(5) Uani 1 1 d . . . H4A H 0.2225 1.0500 0.1958 0.044 Uiso 1 1 calc R . . H4B H 0.2869 1.0512 0.1113 0.044 Uiso 1 1 calc R . . C5 C 0.30045(19) 0.7916(3) 0.17557(14) 0.0353(5) Uani 1 1 d . . . H5 H 0.3220 0.7275 0.1228 0.042 Uiso 1 1 calc R . . C6 C 0.41488(19) 0.8343(5) 0.23681(15) 0.0451(6) Uani 1 1 d . . . H6A H 0.4598 0.9283 0.2086 0.054 Uiso 1 1 calc R . . H6B H 0.4618 0.7184 0.2449 0.054 Uiso 1 1 calc R . . C7 C 0.39416(18) 0.9093(4) 0.32802(15) 0.0418(6) Uani 1 1 d . . . H7A H 0.4697 0.9248 0.3653 0.050 Uiso 1 1 calc R . . H7B H 0.3566 1.0337 0.3209 0.050 Uiso 1 1 calc R . . C8 C 0.31698(18) 0.7749(3) 0.37350(14) 0.0335(5) Uani 1 1 d . . . H8 H 0.3593 0.6538 0.3856 0.040 Uiso 1 1 calc R . . C9 C 0.19917(17) 0.7342(3) 0.31178(13) 0.0302(4) Uani 1 1 d . . . H9 H 0.1621 0.8592 0.2989 0.036 Uiso 1 1 calc R . . C10 C 0.22110(18) 0.6516(3) 0.22013(14) 0.0313(5) Uani 1 1 d . . . C11 C 0.1112(2) 0.6179(4) 0.35768(15) 0.0418(5) Uani 1 1 d . . . H11A H 0.0355 0.6163 0.3197 0.050 Uiso 1 1 calc R . . H11B H 0.1391 0.4871 0.3644 0.050 Uiso 1 1 calc R . . C12 C 0.09302(19) 0.6952(4) 0.44913(14) 0.0395(6) Uani 1 1 d . . . H12A H 0.0522 0.8169 0.4418 0.047 Uiso 1 1 calc R . . H12B H 0.0436 0.6071 0.4768 0.047 Uiso 1 1 calc R . . C13 C 0.21031(18) 0.7215(3) 0.50978(14) 0.0317(5) Uani 1 1 d . . . C14 C 0.28739(17) 0.8547(3) 0.46069(13) 0.0315(5) Uani 1 1 d . . . H14 H 0.2385 0.9677 0.4444 0.038 Uiso 1 1 calc R . . C15 C 0.38404(19) 0.9215(4) 0.53461(14) 0.0422(6) Uani 1 1 d . . . H15A H 0.4395 0.8199 0.5538 0.051 Uiso 1 1 calc R . . H15B H 0.4266 1.0312 0.5163 0.051 Uiso 1 1 calc R . . C16 C 0.30894(18) 0.9739(4) 0.60663(13) 0.0347(5) Uani 1 1 d . . . H16 H 0.2824 1.1067 0.5984 0.042 Uiso 1 1 calc R . . C17 C 0.20011(17) 0.8394(3) 0.59434(14) 0.0319(5) Uani 1 1 d . . . H17 H 0.1283 0.9176 0.5837 0.038 Uiso 1 1 calc R . . C18 C 0.2674(3) 0.5253(4) 0.53161(17) 0.0480(6) Uani 1 1 d . . . H18A H 0.2177 0.4506 0.5642 0.072 Uiso 1 1 calc R . . H18B H 0.3433 0.5423 0.5669 0.072 Uiso 1 1 calc R . . H18C H 0.2771 0.4605 0.4774 0.072 Uiso 1 1 calc R . . C19 C 0.2810(2) 0.4553(4) 0.23216(17) 0.0485(6) Uani 1 1 d . . . H19A H 0.2997 0.4112 0.1759 0.073 Uiso 1 1 calc R . . H19B H 0.2284 0.3661 0.2544 0.073 Uiso 1 1 calc R . . H19C H 0.3522 0.4657 0.2736 0.073 Uiso 1 1 calc R . . C20 C 0.2056(2) 0.7427(4) 0.68628(15) 0.0394(5) Uani 1 1 d . . . H20 H 0.2543 0.6274 0.6862 0.047 Uiso 1 1 calc R . . C21 C 0.0871(2) 0.6848(4) 0.71137(18) 0.0532(7) Uani 1 1 d . . . H21A H 0.0973 0.6415 0.7719 0.080 Uiso 1 1 calc R . . H21B H 0.0542 0.5835 0.6730 0.080 Uiso 1 1 calc R . . H21C H 0.0347 0.7927 0.7051 0.080 Uiso 1 1 calc R . . C22 C 0.27527(19) 0.8904(4) 0.74557(14) 0.0380(5) Uani 1 1 d . . . C23 C 0.3309(2) 0.8208(5) 0.83676(16) 0.0525(7) Uani 1 1 d . . . H23A H 0.3928 0.7296 0.8296 0.063 Uiso 1 1 calc R . . H23B H 0.2714 0.7552 0.8651 0.063 Uiso 1 1 calc R . . C24 C 0.3832(2) 0.9841(5) 0.89702(16) 0.0565(8) Uani 1 1 d . . . H24A H 0.4061 0.9359 0.9568 0.068 Uiso 1 1 calc R . . H24B H 0.4536 1.0324 0.8755 0.068 Uiso 1 1 calc R . . C25 C 0.2960(2) 1.1442(5) 0.89918(16) 0.0488(6) Uani 1 1 d . . . H25 H 0.2292 1.0965 0.9268 0.059 Uiso 1 1 calc R . . C26 C 0.2508(2) 1.2016(4) 0.80437(16) 0.0430(6) Uani 1 1 d . . . H26A H 0.1938 1.3043 0.8047 0.052 Uiso 1 1 calc R . . H26B H 0.3160 1.2487 0.7760 0.052 Uiso 1 1 calc R . . C27 C 0.3484(3) 1.3166(6) 0.95239(19) 0.0729(10) Uani 1 1 d . . . H27A H 0.3813 1.2764 1.0111 0.109 Uiso 1 1 calc R . . H27B H 0.2875 1.4094 0.9564 0.109 Uiso 1 1 calc R . . H27C H 0.4094 1.3725 0.9232 0.109 Uiso 1 1 calc R . . O1 O 0.36589(12) 0.9479(3) 0.69633(9) 0.0411(4) Uani 1 1 d . . . O2 O 0.11912(17) 0.5322(3) 0.07536(12) 0.0407(4) Uani 1 1 d . . . O3 O 0.06458(19) 1.1263(3) 0.06796(12) 0.0515(5) Uani 1 1 d . . . O4 O 0.19631(13) 1.0442(3) 0.75446(10) 0.0388(4) Uani 1 1 d . . . H300 H 0.004(3) 1.104(6) 0.0265(19) 0.059(9) Uiso 1 1 d . . . H200 H 0.111(4) 0.433(8) 0.085(3) 0.095(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0438(11) 0.0201(10) 0.0317(10) 0.0008(9) 0.0026(9) -0.0032(10) C2 0.0351(10) 0.0258(11) 0.0316(10) -0.0031(9) 0.0010(8) 0.0030(9) C3 0.0533(12) 0.0187(10) 0.0321(10) 0.0025(9) 0.0014(9) 0.0035(10) C4 0.0491(12) 0.0227(11) 0.0401(11) 0.0016(10) 0.0086(9) -0.0083(10) C5 0.0389(11) 0.0313(12) 0.0366(11) -0.0063(10) 0.0076(9) -0.0001(10) C6 0.0336(10) 0.0543(16) 0.0484(13) -0.0079(13) 0.0097(9) -0.0051(12) C7 0.0329(10) 0.0503(16) 0.0412(11) -0.0061(11) 0.0016(8) -0.0107(11) C8 0.0331(10) 0.0288(12) 0.0371(11) -0.0006(10) -0.0007(8) -0.0006(9) C9 0.0345(10) 0.0198(10) 0.0344(10) 0.0003(8) -0.0018(8) -0.0001(9) C10 0.0384(10) 0.0182(10) 0.0361(10) -0.0019(9) 0.0014(8) 0.0021(9) C11 0.0437(11) 0.0397(13) 0.0401(11) 0.0004(11) -0.0014(9) -0.0173(11) C12 0.0349(11) 0.0428(14) 0.0401(11) 0.0039(11) 0.0024(9) -0.0114(10) C13 0.0355(10) 0.0228(10) 0.0359(10) 0.0031(9) 0.0015(8) -0.0029(9) C14 0.0311(9) 0.0252(11) 0.0365(10) 0.0004(9) -0.0010(8) -0.0030(9) C15 0.0375(10) 0.0479(15) 0.0404(11) -0.0056(12) 0.0030(9) -0.0112(11) C16 0.0388(10) 0.0285(11) 0.0350(10) -0.0010(10) -0.0008(8) -0.0042(10) C17 0.0327(10) 0.0245(11) 0.0368(11) 0.0047(9) -0.0013(8) 0.0017(9) C18 0.0717(16) 0.0259(13) 0.0451(13) 0.0052(11) 0.0033(11) 0.0089(13) C19 0.0680(15) 0.0243(12) 0.0496(13) -0.0066(12) -0.0042(12) 0.0134(12) C20 0.0512(13) 0.0285(12) 0.0378(11) 0.0054(10) 0.0038(9) 0.0038(11) C21 0.0656(15) 0.0428(16) 0.0522(14) 0.0071(13) 0.0120(12) -0.0094(13) C22 0.0398(11) 0.0378(14) 0.0361(11) 0.0030(10) 0.0039(8) 0.0074(10) C23 0.0592(14) 0.0558(18) 0.0406(13) 0.0093(13) 0.0000(11) 0.0165(14) C24 0.0544(13) 0.079(2) 0.0339(11) 0.0062(14) -0.0026(10) 0.0014(16) C25 0.0513(13) 0.0562(17) 0.0403(12) -0.0026(13) 0.0118(10) -0.0094(14) C26 0.0465(13) 0.0375(13) 0.0460(12) -0.0043(11) 0.0106(10) -0.0024(11) C27 0.090(2) 0.081(3) 0.0475(15) -0.0150(17) 0.0094(14) -0.031(2) O1 0.0382(7) 0.0489(10) 0.0345(7) -0.0027(8) -0.0006(6) 0.0013(8) O2 0.0623(10) 0.0201(8) 0.0372(8) -0.0071(7) -0.0018(7) -0.0036(8) O3 0.0796(13) 0.0175(8) 0.0503(10) 0.0041(8) -0.0157(9) 0.0050(9) O4 0.0383(7) 0.0336(8) 0.0430(8) -0.0010(8) 0.0001(6) 0.0041(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.445(3) . ? C1 C2 1.515(3) . ? C1 C10 1.559(3) . ? C1 H1 0.9800 . ? C2 C3 1.509(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O3 1.437(3) . ? C3 C4 1.509(3) . ? C3 H3 0.9800 . ? C4 C5 1.528(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.524(3) . ? C5 C10 1.553(3) . ? C5 H5 0.9800 . ? C6 C7 1.531(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.520(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C14 1.518(3) . ? C8 C9 1.555(3) . ? C8 H8 0.9800 . ? C9 C11 1.535(3) . ? C9 C10 1.560(3) . ? C9 H9 0.9800 . ? C10 C19 1.534(3) . ? C11 C12 1.531(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.527(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.536(3) . ? C13 C14 1.544(3) . ? C13 C17 1.545(3) . ? C14 C15 1.534(3) . ? C14 H14 0.9800 . ? C15 C16 1.527(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 O1 1.437(3) . ? C16 C17 1.550(3) . ? C16 H16 0.9800 . ? C17 C20 1.545(3) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.512(3) . ? C20 C22 1.520(3) . ? C20 H20 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O1 1.418(3) . ? C22 O4 1.423(3) . ? C22 C23 1.521(3) . ? C23 C24 1.532(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.503(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.515(4) . ? C25 C27 1.527(4) . ? C25 H25 0.9800 . ? C26 O4 1.429(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? O2 H200 0.72(5) . ? O3 H300 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 C2 106.42(17) . . ? O2 C1 C10 111.53(17) . . ? C2 C1 C10 112.31(17) . . ? O2 C1 H1 108.8 . . ? C2 C1 H1 108.8 . . ? C10 C1 H1 108.8 . . ? C3 C2 C1 111.33(17) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? O3 C3 C2 110.68(19) . . ? O3 C3 C4 107.65(18) . . ? C2 C3 C4 110.73(17) . . ? O3 C3 H3 109.2 . . ? C2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C3 C4 C5 113.52(18) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 111.0(2) . . ? C6 C5 C10 111.15(19) . . ? C4 C5 C10 112.64(17) . . ? C6 C5 H5 107.3 . . ? C4 C5 H5 107.3 . . ? C10 C5 H5 107.2 . . ? C5 C6 C7 113.03(17) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 111.9(2) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C14 C8 C7 112.54(19) . . ? C14 C8 C9 108.26(16) . . ? C7 C8 C9 110.34(17) . . ? C14 C8 H8 108.5 . . ? C7 C8 H8 108.5 . . ? C9 C8 H8 108.5 . . ? C11 C9 C8 112.96(17) . . ? C11 C9 C10 113.99(18) . . ? C8 C9 C10 111.84(16) . . ? C11 C9 H9 105.7 . . ? C8 C9 H9 105.7 . . ? C10 C9 H9 105.7 . . ? C19 C10 C5 109.81(18) . . ? C19 C10 C1 107.61(18) . . ? C5 C10 C1 108.87(17) . . ? C19 C10 C9 110.50(19) . . ? C5 C10 C9 109.38(17) . . ? C1 C10 C9 110.63(16) . . ? C12 C11 C9 113.9(2) . . ? C12 C11 H11A 108.8 . . ? C9 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C9 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 111.75(18) . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C18 109.5(2) . . ? C12 C13 C14 107.05(17) . . ? C18 C13 C14 112.92(19) . . ? C12 C13 C17 113.82(17) . . ? C18 C13 C17 112.15(18) . . ? C14 C13 C17 101.18(17) . . ? C8 C14 C15 121.68(18) . . ? C8 C14 C13 114.28(19) . . ? C15 C14 C13 103.38(17) . . ? C8 C14 H14 105.4 . . ? C15 C14 H14 105.4 . . ? C13 C14 H14 105.4 . . ? C16 C15 C14 100.27(17) . . ? C16 C15 H15A 111.7 . . ? C14 C15 H15A 111.7 . . ? C16 C15 H15B 111.7 . . ? C14 C15 H15B 111.7 . . ? H15A C15 H15B 109.5 . . ? O1 C16 C15 115.08(18) . . ? O1 C16 C17 106.67(17) . . ? C15 C16 C17 106.88(19) . . ? O1 C16 H16 109.3 . . ? C15 C16 H16 109.3 . . ? C17 C16 H16 109.3 . . ? C13 C17 C20 121.3(2) . . ? C13 C17 C16 105.76(16) . . ? C20 C17 C16 103.10(16) . . ? C13 C17 H17 108.7 . . ? C20 C17 H17 108.7 . . ? C16 C17 H17 108.7 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C22 116.5(2) . . ? C21 C20 C17 114.9(2) . . ? C22 C20 C17 100.90(18) . . ? C21 C20 H20 108.0 . . ? C22 C20 H20 108.0 . . ? C17 C20 H20 108.0 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O1 C22 O4 110.8(2) . . ? O1 C22 C20 103.96(18) . . ? O4 C22 C20 106.49(18) . . ? O1 C22 C23 109.18(19) . . ? O4 C22 C23 110.2(2) . . ? C20 C22 C23 116.0(2) . . ? C22 C23 C24 112.6(2) . . ? C22 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? C22 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C25 C24 C23 111.4(2) . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C24 C25 C26 108.4(2) . . ? C24 C25 C27 112.9(2) . . ? C26 C25 C27 110.5(3) . . ? C24 C25 H25 108.3 . . ? C26 C25 H25 108.3 . . ? C27 C25 H25 108.3 . . ? O4 C26 C25 111.4(2) . . ? O4 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? O4 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 O1 C16 105.59(16) . . ? C1 O2 H200 103(4) . . ? C3 O3 H300 105(3) . . ? C22 O4 C26 113.47(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -63.9(2) . . . . ? C10 C1 C2 C3 58.4(2) . . . . ? C1 C2 C3 O3 -175.99(16) . . . . ? C1 C2 C3 C4 -56.7(2) . . . . ? O3 C3 C4 C5 175.16(18) . . . . ? C2 C3 C4 C5 54.1(2) . . . . ? C3 C4 C5 C6 -177.66(17) . . . . ? C3 C4 C5 C10 -52.3(2) . . . . ? C4 C5 C6 C7 71.3(3) . . . . ? C10 C5 C6 C7 -54.9(3) . . . . ? C5 C6 C7 C8 54.8(3) . . . . ? C6 C7 C8 C14 -175.38(19) . . . . ? C6 C7 C8 C9 -54.3(3) . . . . ? C14 C8 C9 C11 -49.9(3) . . . . ? C7 C8 C9 C11 -173.4(2) . . . . ? C14 C8 C9 C10 179.94(18) . . . . ? C7 C8 C9 C10 56.4(2) . . . . ? C6 C5 C10 C19 -66.5(2) . . . . ? C4 C5 C10 C19 168.22(18) . . . . ? C6 C5 C10 C1 175.92(18) . . . . ? C4 C5 C10 C1 50.6(2) . . . . ? C6 C5 C10 C9 54.9(2) . . . . ? C4 C5 C10 C9 -70.4(2) . . . . ? O2 C1 C10 C19 -53.9(2) . . . . ? C2 C1 C10 C19 -173.23(19) . . . . ? O2 C1 C10 C5 65.1(2) . . . . ? C2 C1 C10 C5 -54.3(2) . . . . ? O2 C1 C10 C9 -174.67(18) . . . . ? C2 C1 C10 C9 66.0(2) . . . . ? C11 C9 C10 C19 -65.0(2) . . . . ? C8 C9 C10 C19 64.6(2) . . . . ? C11 C9 C10 C5 173.98(18) . . . . ? C8 C9 C10 C5 -56.4(2) . . . . ? C11 C9 C10 C1 54.1(2) . . . . ? C8 C9 C10 C1 -176.28(17) . . . . ? C8 C9 C11 C12 48.9(3) . . . . ? C10 C9 C11 C12 177.96(19) . . . . ? C9 C11 C12 C13 -52.6(3) . . . . ? C11 C12 C13 C18 -66.4(3) . . . . ? C11 C12 C13 C14 56.3(3) . . . . ? C11 C12 C13 C17 167.2(2) . . . . ? C7 C8 C14 C15 -54.1(3) . . . . ? C9 C8 C14 C15 -176.3(2) . . . . ? C7 C8 C14 C13 -179.28(17) . . . . ? C9 C8 C14 C13 58.5(2) . . . . ? C12 C13 C14 C8 -62.2(2) . . . . ? C18 C13 C14 C8 58.4(2) . . . . ? C17 C13 C14 C8 178.43(17) . . . . ? C12 C13 C14 C15 163.47(19) . . . . ? C18 C13 C14 C15 -76.0(2) . . . . ? C17 C13 C14 C15 44.0(2) . . . . ? C8 C14 C15 C16 -176.6(2) . . . . ? C13 C14 C15 C16 -46.5(2) . . . . ? C14 C15 C16 O1 149.0(2) . . . . ? C14 C15 C16 C17 30.8(2) . . . . ? C12 C13 C17 C20 105.1(2) . . . . ? C18 C13 C17 C20 -19.9(3) . . . . ? C14 C13 C17 C20 -140.45(19) . . . . ? C12 C13 C17 C16 -138.35(19) . . . . ? C18 C13 C17 C16 96.7(2) . . . . ? C14 C13 C17 C16 -23.9(2) . . . . ? O1 C16 C17 C13 -127.89(18) . . . . ? C15 C16 C17 C13 -4.3(2) . . . . ? O1 C16 C17 C20 0.4(2) . . . . ? C15 C16 C17 C20 124.0(2) . . . . ? C13 C17 C20 C21 -91.7(3) . . . . ? C16 C17 C20 C21 150.4(2) . . . . ? C13 C17 C20 C22 142.19(19) . . . . ? C16 C17 C20 C22 24.3(2) . . . . ? C21 C20 C22 O1 -167.2(2) . . . . ? C17 C20 C22 O1 -42.2(2) . . . . ? C21 C20 C22 O4 -50.2(3) . . . . ? C17 C20 C22 O4 74.9(2) . . . . ? C21 C20 C22 C23 72.9(3) . . . . ? C17 C20 C22 C23 -162.0(2) . . . . ? O1 C22 C23 C24 71.6(3) . . . . ? O4 C22 C23 C24 -50.3(3) . . . . ? C20 C22 C23 C24 -171.4(2) . . . . ? C22 C23 C24 C25 50.1(3) . . . . ? C23 C24 C25 C26 -52.5(3) . . . . ? C23 C24 C25 C27 -175.2(2) . . . . ? C24 C25 C26 O4 58.6(3) . . . . ? C27 C25 C26 O4 -177.3(2) . . . . ? O4 C22 O1 C16 -69.9(2) . . . . ? C20 C22 O1 C16 44.2(2) . . . . ? C23 C22 O1 C16 168.6(2) . . . . ? C15 C16 O1 C22 -145.8(2) . . . . ? C17 C16 O1 C22 -27.4(2) . . . . ? O1 C22 O4 C26 -64.0(2) . . . . ? C20 C22 O4 C26 -176.40(17) . . . . ? C23 C22 O4 C26 57.0(3) . . . . ? C25 C26 O4 C22 -62.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.266 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.048